#1
Friday, October 2, 2026, 7:30 PM; Saturday, October 3, 7:00 PM and 10:00 PM
Bill Burr Live
Bill Burr, host of the Monday Morning Podcast and creator of specials including Paper Tiger, takes his stand-up to the Chicago Theatre.
One Weekend Only
Date night in West Loop, Chicago the Weekend of Oct 2–4, 2026
Stumblday's hand-checked ranking of the best date night in West Loop, Chicago, Downtown, the Loop & West Loop the weekend of Oct 2–4, 2026: 24 picks.
24 picks · checked Sep 21
24 picks
#1Friday, October 2, 2026, 7:30 PM; Saturday, October 3, 7:00 PM and 10:00 PM · One Weekend Only
Bill Burr Live
Bill Burr, host of the Monday Morning Podcast and creator of specials including Paper Tiger, takes his stand-up to the Chicago Theatre.
Add to calendar#2
CIBC Theatre, 18 West Monroe, Downtown, the Loop & West LoopFriday, October 2, 7 p.m.; Saturday, October 3, 2 and 7:30 p.m.; Sunday, October 4, 1 and 6:30 p.m.
Operation Mincemeat (Chicago)
Operation Mincemeat turns a bizarre Second World War deception plot into a musical comedy at the CIBC Theatre.
One Weekend Only
#2Friday, October 2, 7 p.m.; Saturday, October 3, 2 and 7:30 p.m.; Sunday, October 4, 1 and 6:30 p.m. · One Weekend Only
CIBC Theatre, 18 West Monroe, Downtown, the Loop & West LoopOperation Mincemeat (Chicago)
Operation Mincemeat turns a bizarre Second World War deception plot into a musical comedy at the CIBC Theatre.
Add to calendar#3
Goodman Albert Theatre, Downtown, the Loop & West LoopMichel Curi · CC BY 2.0 · Wikimedia CommonsThrough Oct 4, 2026
The Attic
The 7 Fingers turn a former trapezist's memoir into daring aerial theater, running into October.
Limited Run
#3Through Oct 4, 2026 · Limited Run
Goodman Albert Theatre, Downtown, the Loop & West LoopMichel Curi · CC BY 2.0 · Wikimedia CommonsThe Attic
The 7 Fingers turn a former trapezist's memoir into daring aerial theater, running into October.
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Friday, October 2, 7 and 9:15 p.m.; Saturday, October 3, 7 and 9:15 p.m.
Ali Macofsky
Ali Macofsky headlines four Zanies sets across Friday and Saturday night.
One Weekend Only
#4Friday, October 2, 7 and 9:15 p.m.; Saturday, October 3, 7 and 9:15 p.m. · One Weekend Only
Ali Macofsky
Ali Macofsky headlines four Zanies sets across Friday and Saturday night.
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#5
Columbia College Chicago Dance Center, Downtown, the Loop & West LoopBeyond My Ken · CC BY-SA 4.0 · Wikimedia CommonsFri, Oct 2, 2026 · 7:30pm$35
Cerqua Rivera Dance Theatre Presents the Second Chicago Latinx/e Contemporary Movement Festival at the Dance Center of Columbia College
Cerqua Rivera hosts a Latinx/e contemporary movement festival at the Dance Center for $35.
One Day Only
#5Fri, Oct 2, 2026 · 7:30pm · One Day Only
Columbia College Chicago Dance Center, Downtown, the Loop & West LoopBeyond My Ken · CC BY-SA 4.0 · Wikimedia CommonsCerqua Rivera Dance Theatre Presents the Second Chicago Latinx/e Contemporary Movement Festival at the Dance Center of Columbia College
Cerqua Rivera hosts a Latinx/e contemporary movement festival at the Dance Center for $35.
Add to calendar#6
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopSeptember 11–October 18, 2026; selected performances
Play On! — Chicago Shakespeare Theater
Duke Ellington’s music carries Twelfth Night’s disguises and romantic mix-ups into 1930s Harlem in Play On!
Limited Run
#6September 11–October 18, 2026; selected performances · Limited Run
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopPlay On! — Chicago Shakespeare Theater
Duke Ellington’s music carries Twelfth Night’s disguises and romantic mix-ups into 1930s Harlem in Play On!
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Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West Loopw_lemay · CC BY-SA 2.0 · Wikimedia CommonsThrough November 8, 2026
Jekyll & Hyde
Kokandy's 10-time Jeff-nominated musical revival, back after a sold-out, extended Chicago run.
Limited Run
#7Through November 8, 2026 · Limited Run
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West Loopw_lemay · CC BY-SA 2.0 · Wikimedia CommonsJekyll & Hyde
Kokandy's 10-time Jeff-nominated musical revival, back after a sold-out, extended Chicago run.
Add to calendar#8
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsSunday 4:15pm
ACE IN THE Hole
Catch this film screening at the Gene Siskel Film Center afternoon.
Limited Run
#8Sunday 4:15pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia Commons#9
Northerly Island Park, South Loop, Downtown, the Loop & West LoopFriday, October 2, 2026, 7–8:40 p.m.; dusk start is approximateFree
Campfire Horrors: The Rocky Horror Picture Show
Watch the cult musical outdoors by a campfire on Northerly Island's lakefront.
FreeOne Day Only
#9Friday, October 2, 2026, 7–8:40 p.m.; dusk start is approximate · One Day Only
Northerly Island Park, South Loop, Downtown, the Loop & West LoopCampfire Horrors: The Rocky Horror Picture Show
Watch the cult musical outdoors by a campfire on Northerly Island's lakefront.
Add to calendar#10
Goodman Theatre, Owen Theatre, The Loop, Downtown, the Loop & West LoopSeptember 26 – November 1, 2026From $29 including fees
Dead Girl's Quinceañera
Dead Girl's Quinceañera has enough weekend energy to earn a spot on the board.
Limited Run
#10September 26 – November 1, 2026 · Limited Run
Goodman Theatre, Owen Theatre, The Loop, Downtown, the Loop & West LoopDead Girl's Quinceañera
Dead Girl's Quinceañera has enough weekend energy to earn a spot on the board.
Add to calendar#11
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopExtended through November 15, 2026; 75-minute timed performances
Theater of the Mind
Theater of the Mind has enough weekend energy to earn a spot on the board.
Limited Run
#11Extended through November 15, 2026; 75-minute timed performances · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopTheater of the Mind
Theater of the Mind has enough weekend energy to earn a spot on the board.
Add to calendar#12
The Comedy Bar, Downtown, the Loop & West LoopFri, Oct 2, 2026 · 9:00pm$25 – $35
Chicago’s Best Comedy Show at The Comedy Bar
Chicago’s Best Comedy Show at The Comedy Bar has enough weekend energy to earn a spot on the board.
One Weekend Only
#12Fri, Oct 2, 2026 · 9:00pm · One Weekend Only
The Comedy Bar, Downtown, the Loop & West LoopChicago’s Best Comedy Show at The Comedy Bar
Chicago’s Best Comedy Show at The Comedy Bar has enough weekend energy to earn a spot on the board.
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The Comedy Bar, Downtown, the Loop & West LoopSat, Oct 3, 2026 · 7:00pm$25 – $35
Dauood Naimyar at The Comedy Bar
Comedian Dauood Naimyar, a Just For Laughs New Face, does stand-up at The Comedy Bar.
One Day Only
#13Sat, Oct 3, 2026 · 7:00pm · One Day Only
The Comedy Bar, Downtown, the Loop & West LoopDauood Naimyar at The Comedy Bar
Comedian Dauood Naimyar, a Just For Laughs New Face, does stand-up at The Comedy Bar.
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The Comedy Bar, Downtown, the Loop & West LoopSun, Oct 4, 2026 · 8:00pm$30 – $40
Justin Whitehead at The Comedy Bar
Comedian and content creator Justin Whitehead does stand-up at The Comedy Bar.
One Day Only
#14Sun, Oct 4, 2026 · 8:00pm · One Day Only
The Comedy Bar, Downtown, the Loop & West LoopJustin Whitehead at The Comedy Bar
Comedian and content creator Justin Whitehead does stand-up at The Comedy Bar.
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The Comedy Bar, Downtown, the Loop & West LoopSun, Oct 4, 2026 · 6:00pm$30 – $40
Kevin Williams at The Comedy Bar
Kevin Williams, a BET Comic View regular, does stand-up at The Comedy Bar.
One Day Only
#15Sun, Oct 4, 2026 · 6:00pm · One Day Only
The Comedy Bar, Downtown, the Loop & West LoopKevin Williams at The Comedy Bar
Kevin Williams, a BET Comic View regular, does stand-up at The Comedy Bar.
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Gene Siskel Film Center, Downtown, the Loop & West Loop#16Sunday 2pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West Loop#17
Zanies Chicago, Old Town, Downtown, the Loop & West LoopSunday, October 4, 2026; doors 3 p.m., show 4 p.m.$29
Parkinson’s Foundation Special Event
Chicago comics raise money for Parkinson's Foundation at a special Sunday show.
Limited Run
#17Sunday, October 4, 2026; doors 3 p.m., show 4 p.m. · Limited Run
Zanies Chicago, Old Town, Downtown, the Loop & West LoopParkinson’s Foundation Special Event
Chicago comics raise money for Parkinson's Foundation at a special Sunday show.
Add to calendar#18
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopFri, Oct 2, 2026 · 7:00pm
Drunk Shakespeare: Drunk Dracula (21+ Event)
Drunk Shakespeare: Drunk Dracula (21+ Event) has enough weekend energy to earn a spot on the board.
Limited Run
#18Fri, Oct 2, 2026 · 7:00pm · Limited Run
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopDrunk Shakespeare: Drunk Dracula (21+ Event)
Drunk Shakespeare: Drunk Dracula (21+ Event) has enough weekend energy to earn a spot on the board.
Add to calendar#19
Gene Siskel Film Center, Downtown, the Loop & West LoopFriday 6pm
Gremlins 2: THE NEW Batch
Gremlins 2: THE NEW Batch has enough weekend energy to earn a spot on the board.
Limited Run
#19Friday 6pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopGremlins 2: THE NEW Batch
Gremlins 2: THE NEW Batch has enough weekend energy to earn a spot on the board.
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Gene Siskel Film Center, Downtown, the Loop & West Loop#20Sunday 12pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West Loop#21
Gene Siskel Film Center, Downtown, the Loop & West Loop#21Friday 8:45pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West Loop#22
Gene Siskel Film Center, Downtown, the Loop & West LoopSaturday 2pm
HOW TO Marry A Millionaire
HOW TO Marry A Millionaire has enough weekend energy to earn a spot on the board.
Limited Run
#22Saturday 2pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopHOW TO Marry A Millionaire
HOW TO Marry A Millionaire has enough weekend energy to earn a spot on the board.
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Reggies Bananna's Shack, 2105 South State Street, Downtown, the Loop & West LoopFri, Oct 2, 2026 · 8:00pm
Dale McPeek and Very Special Guests!
Dale McPeek and Very Special Guests! has enough weekend energy to earn a spot on the board.
Limited Run
#23Fri, Oct 2, 2026 · 8:00pm · Limited Run
Reggies Bananna's Shack, 2105 South State Street, Downtown, the Loop & West LoopDale McPeek and Very Special Guests!
Dale McPeek and Very Special Guests! has enough weekend energy to earn a spot on the board.
Add to calendar#24
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopSeptember 15 – October 25, 2026Ticketed via Lookingglass The…
Kowalski
Kowalski has enough weekend energy to earn a spot on the board.
Limited Run
#24September 15 – October 25, 2026 · Limited Run
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West Loop